We proposed to apply controlled-potential electrooxidation to the study of indole alkaloid synthesis and biosynthesis. Indole derivatives will be selected for study, based upon their importance as therapeutic agents, their role in alkaloid biosynthesis, their importance as synthetic intermediates, and their intrinsic chemistry. Preliminary electroanalytical studies will be made as a guide to the selection of experimental conditions for preparative oxidation experiments. Simultaneous, intensive, mechanistic studies and coordinated, preparative studies will then be made of the compounds selected. Finally, we hope to discover new reactions and new methods of synthesis for indole alkaloids. We also hope to broaden the scope of preparative organic electrochemistry to include these beautifully complex molecules. Specifically, we will study catharanthine and vindoline, and their conversion to the dimeric, antileukemic drugs, vinblastine and vincristine. We will also look at an extensive series of other indole derivatives.